Synfacts 2008(10): 1069-1069  
DOI: 10.1055/s-2008-1078131
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Intermolecular 1,3-Dipolar Cycloaddition

Contributor(s): Mark Lautens, Frédéric Ménard
N. Shimada, M. Anada, S. Nakamura, H. Nambu, H. Tsutsui, S. Hashimoto*
Hokkaido University, Sapporo, Japan
Further Information

Publication History

Publication Date:
22 September 2008 (online)

Significance

Carbon ylide cycloadditions have proven utility in total synthesis to build complex structures rapidly. The authors have designed a chiral catalyst that overcomes previous limitations which restricted the reaction to electron-deficient dipolarophiles (S.-i. Hashimoto and co-workers J. Am. Chem. Soc. 1999, 121, 1417). High enantioselectivity in intermolecular reactions allows the synthesis of complex chiral oxabicyclic structures.